Water → HCID 15571967, compound

HRID 1954140Notes

Reaction equation

HRID 1954140 reaction equation
[H-].[Na+].[NH:3]1[C:14](=[O:15])[C:13]2[N:11]([CH3:12])[CH:10]=[N:9][C:8]=2[N:6]([CH3:7])[C:4]1=[O:5].Br[CH2:17][CH2:18][CH:19]=[CH2:20].O>CS(C)=O>[CH2:20]([N:3]1[C:14](=[O:15])[C:13]2[N:11]([CH3:12])[CH:10]=[N:9][C:8]=2[N:6]([CH3:7])[C:4]1=[O:5])[CH2:19][CH:18]=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 21241Homoallyl bromideHCID 24758Sodium hydride

Product 1

HCID 15571967HCID 15571967, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This example illustrates a synthesis of 1-(3,4-Oxidobutyl)-3,7-dimethylxanthine (inventive compound no. 2513). Sodium hydride (95%) (1.26 g, 50 mmol) was added to a solution of theobromine (7.2 g, 40 mmol) in dimethylsulfoxide (300 mL). After 20 minutes of stirring, 4-bromobutene (5.4 g, 40 mmol) was added. After 16 hours of stirring at room temperature, the reaction was poured into a separatory funnel containing 1 L of water and extracted with dichloromethane (5×200 mL). The organic extracts were combined, washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using a 20% petroleum ether/ethyl acetate eluant to yield 6.3 g (67.7% yield) 1-(3-Butenyl)-3,7-dimethylxanthine (inventive compound no. 2503) as a white solid.

Workup

  1. stirringAfter 16 hours of stirring at room temperature
  2. additionthe reaction was poured into a separatory funnel
  3. extractionextracted with dichloromethane (5×200 mL)
  4. washwashed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product obtained
  8. customwas further purified by flash chromatography over silica gel using a 20% petroleum ether/ethyl acetate eluant

Sources & evidence

ORD record
ord-ec9444a3adab44c0b6c626fea5d2241d
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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